ORGN 591 |
| Trilobin and Trilobacin, members of a biologically active class of compounds called Annonaceous Acetogenins, exhibit potent antitumor activity. The core of these two molecules contains cis/erythro/trans relative configurations about bis-tetrahydrofuran rings, as in compound 3. This core was achieved starting from meso-diol 1 via the ring opening/cross metathesis utilizing Grubbs' 2nd generation ruthenium benzylidene catalyst and 1,4-diacetoxy-cis-2-butene as the coupling partner. This was followed by Pd(0) mediated double cycloetherification using Trost's (R,R)-DPPBA ligand, yielding the desired desymmetrized bis-tetrahydrofuran core 3. Progress toward the differentiation of the two vinyl groups in 3 followed by side-chain elaboration leading to the natural products Trilobin and Trilobacin will be discussed.
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New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster
Sci-Mix
Division of Organic Chemistry |
